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Literature DB >> 23253097

Enantioselective synthesis of planar chiral ferrocenes via palladium-catalyzed direct coupling with arylboronic acids.

De-Wei Gao¹, Yan-Chao Shi, Qing Gu, Zheng-Le Zhao, Shu-Li You.

Abstract

Enantioselective Pd(II)-catalyzed direct coupling of aminomethylferrocene derivatives with boronic acids was realized. With commercially available Boc-L-Val-OH as a ligand, planar-chiral ferrocenes could be synthesized in yields of 14-81% with up to 99% ee under mild conditions.

Entities: Chemical

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Year: 2012 PMID： 23253097 DOI： 10.1021/ja311082u

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

28 in total

Review 1. Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

Authors: Alan H Cherney; Nathaniel T Kadunce; Sarah E Reisman
Journal: Chem Rev Date: 2015-08-13 Impact factor: 60.622

2. Ligand-Accelerated ortho-C-H Olefination of Phenylacetic Acids.

Authors: Keary M Engle; Navid Dastbaravardeh; Peter S Thuy-Boun; Dong-Hui Wang; Aaron C Sather; Jin-Quan Yu
Journal: Organic Synth Date: 2015-03-12

3. Palladium(II)-Catalyzed Site-Selective C(sp³ )-H Alkynylation of Oligopeptides: A Linchpin Approach for Oligopeptide-Drug Conjugation.

Authors: Tao Liu; Jennifer X Qiao; Michael A Poss; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2017-08-07 Impact factor: 15.336

4. Palladium-Catalyzed C-H Arylation Using Aryltrifluoroborates in Conjunction with a Mn^III Oxidant under Mild Conditions.

Authors: Cydney K Seigerman; Tiffiny M Micyus; Sharon R Neufeldt; Melanie S Sanford
Journal: Tetrahedron Date: 2013-07-08 Impact factor: 2.457

Enantioselective synthesis of planar chiral ferrocenes via palladium-catalyzed direct coupling with arylboronic acids.

Review 1. Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

2. Ligand-Accelerated ortho-C-H Olefination of Phenylacetic Acids.

3. Palladium(II)-Catalyzed Site-Selective C(sp³ )-H Alkynylation of Oligopeptides: A Linchpin Approach for Oligopeptide-Drug Conjugation.

4. Palladium-Catalyzed C-H Arylation Using Aryltrifluoroborates in Conjunction with a Mn^III Oxidant under Mild Conditions.

5. Enantioselective γ-C(sp³)-H Activation of Alkyl Amines via Pd(II)/Pd(0) Catalysis.

6. Kinetic Resolution of Benzylamines via Palladium(II)-Catalyzed C-H Cross-Coupling.

7. Palladium(II)-catalyzed highly enantioselective C-H arylation of cyclopropylmethylamines.

8. Enantioselective remote meta-C-H arylation and alkylation via a chiral transient mediator.

9. Ligand-Promoted C(sp(3) )-H Olefination en Route to Multi-functionalized Pyrazoles.

10. Enantioselective C-H Olefination of α-Hydroxy and α-Amino Phenylacetic Acids by Kinetic Resolution.